In an attempt to develop biologically active compounds from the inactive tr
ans isomer (3a) of stilbene la, after asymmetric dihydroxylation to optical
ly pure (R,R)-diol 8 the unexpected racemic diphenylacetaldehyde (9) was ge
nerated via a Pinacol rearrangement. Several derivatives of diphenylacetald
ehyde 9 were synthesized (11-15) and reported. Further reaction of aldehyde
9 during desilylation through autoxidative decarbonylation afforded benzop
henone 2b, designated hydroxyphenstatin, a potent antitumor and antimitotic
agent. Hydroxyphenstatin showed potent inhibition of the tubulin assembly
(IC50 0.82 muM) and exhibited an ED50 of 2.5 mug/mL against the P388 lympho
cytic leukemia cell line.